1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide

HRID 1177941

반응식

HRID 1177941 반응식
CCN(C(C)C)C(C)C.[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)#[CH:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:42][CH2:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:52](=[O:64])[C:53]2[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=2[C:60]([F:63])([F:62])[F:61])[CH2:48][CH2:47]1)=[O:45]>CN(C=O)C.O>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:42][CH2:43][C:44]([N:46]2[CH2:47][CH2:48][N:49]([C:52](=[O:64])[C:53]3[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=3[C:60]([F:62])([F:61])[F:63])[CH2:50][CH2:51]2)=[O:45])=[O:18])=[CH:19][CH:20]=1)#[CH:11]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5897064-Ethynylbenzoic acidHCID 595595982-Amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone

생성물 1

HCID 595595974-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide수율 41.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (263.67 mg, 0.34 mL, 2.04 mmol) was added to a stirred solution of 4-Ethynyl-benzoic acid (100 mg, 0.68 mmol) in DMF (1.5 mL). HOBT (92 mg, 0.68 mmol) and EDCI (156.42 mg, 0.81 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (253 mg, 0.68 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with 5% sodium bicarbonate solution followed by brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was recrystallized from a mixture of EtOAc and ether to afford 130 mg (41.1% yield) of 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide. LCMS Purity: 87.29%. 1H NMR (DMSO-d6): δ 8.7 (m, 1H), 8.0-7.8 (m, 3H), 7.6-7.4 (m, 4H), 4.4 (s, 1H), 4.2-4.1 (m, 2H), 3.8-3.4 (m, 3H), 3.2-3.0 (m, 2H).

후처리

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with 5% sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was recrystallized from a mixture of EtOAc and ether

출처 및 근거

ORD 기록
ord-afd866c37f594f5b806299fae29cb8cd
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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